NPASS Compound

Structure

NPC45033 OpenBabel07101719512D 29 30 0 0 0 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 20 27 2 0 0 0 0 23 25 2 3 0 0 0 23 28 1 0 0 0 0 24 26 1 0 0 0 0 24 29 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.21
Volume:	428.547
LogP:	3.349
LogD:	3.295
LogS:	-4.38
# Rotatable Bonds:	13
TPSA:	66.48
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.496
Synthetic Accessibility Score:	2.247
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041
MDCK Permeability:	2.7441805286798626e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	94.31897735595703%
Volume Distribution (VD):	0.394
Pgp-substrate:	4.8836445808410645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.408
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.924
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.505
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	3.698
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.494
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.266
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.835
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.009

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC45033

Natural Product ID:	NPC45033
*Common Name:**	Edulimide
IUPAC Name:	N-acetyl-3-phenyl-N-[4-[[(E)-3-phenylprop-2-enoyl]amino]butyl]propanamide
Synonyms:	Edulimide
Standard InCHIKey:	JEZVLNLOENILMI-JQIJEIRASA-N
Standard InCHI:	InChI=1S/C24H28N2O3/c1-20(27)26(24(29)17-15-22-12-6-3-7-13-22)19-9-8-18-25-23(28)16-14-21-10-4-2-5-11-21/h2-7,10-14,16H,8-9,15,17-19H2,1H3,(H,25,28)/b16-14+
SMILES:	OC(=NCCCCN(C(=O)CCc1ccccc1)C(=O)C)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464783
PubChem CID:	10548550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002810] Cinnamic acid amides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775404]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496701]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868148]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	>	250.0	ug/g	PMID[495112]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	>	250.0	ug/g	PMID[495112]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC45033 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	104
0.1-0.2	1731
0.2-0.3	7980
0.3-0.4	15156
0.4-0.5	14534
0.5-0.6	2547
0.6-0.7	582
0.7-0.8	60
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC220698
0.8148	Intermediate Similarity	NPC471447
0.8056	Intermediate Similarity	NPC473418
0.8053	Intermediate Similarity	NPC33742
0.798	Intermediate Similarity	NPC203076
0.7965	Intermediate Similarity	NPC276949
0.7965	Intermediate Similarity	NPC35850
0.7885	Intermediate Similarity	NPC256452
0.7845	Intermediate Similarity	NPC470545
0.7778	Intermediate Similarity	NPC470546
0.7759	Intermediate Similarity	NPC470544
0.7658	Intermediate Similarity	NPC473498
0.7647	Intermediate Similarity	NPC27833
0.7619	Intermediate Similarity	NPC71140
0.7607	Intermediate Similarity	NPC315276
0.7607	Intermediate Similarity	NPC14672
0.7607	Intermediate Similarity	NPC285926
0.7583	Intermediate Similarity	NPC71684
0.7576	Intermediate Similarity	NPC14326
0.7549	Intermediate Similarity	NPC473031
0.7525	Intermediate Similarity	NPC3210
0.75	Intermediate Similarity	NPC200964
0.7478	Intermediate Similarity	NPC475013
0.7455	Intermediate Similarity	NPC329375
0.744	Intermediate Similarity	NPC111428
0.744	Intermediate Similarity	NPC473322
0.7411	Intermediate Similarity	NPC143516
0.7407	Intermediate Similarity	NPC472258
0.7381	Intermediate Similarity	NPC200589
0.735	Intermediate Similarity	NPC476048
0.7345	Intermediate Similarity	NPC474804
0.7345	Intermediate Similarity	NPC191215
0.7345	Intermediate Similarity	NPC274089
0.7345	Intermediate Similarity	NPC474973
0.7345	Intermediate Similarity	NPC130898
0.7323	Intermediate Similarity	NPC255447
0.7311	Intermediate Similarity	NPC239357
0.7302	Intermediate Similarity	NPC469666
0.7257	Intermediate Similarity	NPC167336
0.7248	Intermediate Similarity	NPC33168
0.7241	Intermediate Similarity	NPC319579
0.7232	Intermediate Similarity	NPC471317
0.7212	Intermediate Similarity	NPC17497
0.7212	Intermediate Similarity	NPC305602
0.72	Intermediate Similarity	NPC101719
0.7184	Intermediate Similarity	NPC123476
0.7177	Intermediate Similarity	NPC474082
0.7177	Intermediate Similarity	NPC175726
0.717	Intermediate Similarity	NPC172128
0.7168	Intermediate Similarity	NPC275467
0.7132	Intermediate Similarity	NPC257390
0.712	Intermediate Similarity	NPC222466
0.7117	Intermediate Similarity	NPC12730
0.7083	Intermediate Similarity	NPC473573
0.7069	Intermediate Similarity	NPC473676
0.7063	Intermediate Similarity	NPC4974
0.7054	Intermediate Similarity	NPC120251
0.704	Intermediate Similarity	NPC6975
0.7037	Intermediate Similarity	NPC473661
0.7007	Intermediate Similarity	NPC16188
0.6992	Remote Similarity	NPC132636
0.6981	Remote Similarity	NPC262393
0.6957	Remote Similarity	NPC9373
0.6937	Remote Similarity	NPC311242
0.6935	Remote Similarity	NPC302169
0.693	Remote Similarity	NPC202613
0.693	Remote Similarity	NPC164859
0.6903	Remote Similarity	NPC469457
0.6887	Remote Similarity	NPC471638
0.688	Remote Similarity	NPC202521
0.6875	Remote Similarity	NPC322598
0.6866	Remote Similarity	NPC242159
0.6866	Remote Similarity	NPC313694
0.685	Remote Similarity	NPC285394
0.6842	Remote Similarity	NPC118099
0.6842	Remote Similarity	NPC474787
0.6842	Remote Similarity	NPC474855
0.6842	Remote Similarity	NPC9687
0.6842	Remote Similarity	NPC90194
0.6842	Remote Similarity	NPC475318
0.6842	Remote Similarity	NPC293377
0.6842	Remote Similarity	NPC473360
0.6842	Remote Similarity	NPC76785
0.6842	Remote Similarity	NPC79465
0.6842	Remote Similarity	NPC476102
0.6842	Remote Similarity	NPC49577
0.6842	Remote Similarity	NPC260045
0.6842	Remote Similarity	NPC273907
0.6842	Remote Similarity	NPC474811
0.6842	Remote Similarity	NPC475598
0.6842	Remote Similarity	NPC151706
0.6838	Remote Similarity	NPC55529
0.6838	Remote Similarity	NPC161069
0.6833	Remote Similarity	NPC474584
0.6827	Remote Similarity	NPC474088
0.6822	Remote Similarity	NPC12429
0.6818	Remote Similarity	NPC474974
0.681	Remote Similarity	NPC211551
0.6809	Remote Similarity	NPC233702
0.68	Remote Similarity	NPC80150
0.68	Remote Similarity	NPC476990
0.6791	Remote Similarity	NPC127741
0.6789	Remote Similarity	NPC245259
0.6786	Remote Similarity	NPC254798
0.678	Remote Similarity	NPC96224
0.678	Remote Similarity	NPC24101
0.6769	Remote Similarity	NPC150863
0.6767	Remote Similarity	NPC474473
0.6767	Remote Similarity	NPC248283
0.6765	Remote Similarity	NPC272260
0.6761	Remote Similarity	NPC202198
0.6759	Remote Similarity	NPC470877
0.6757	Remote Similarity	NPC303045
0.6757	Remote Similarity	NPC161972
0.6752	Remote Similarity	NPC327481
0.6744	Remote Similarity	NPC136453
0.6744	Remote Similarity	NPC477937
0.6741	Remote Similarity	NPC316906
0.6739	Remote Similarity	NPC471680
0.6739	Remote Similarity	NPC209509
0.6733	Remote Similarity	NPC9796
0.6723	Remote Similarity	NPC65855
0.6723	Remote Similarity	NPC292758
0.6719	Remote Similarity	NPC22746
0.6697	Remote Similarity	NPC471307
0.6697	Remote Similarity	NPC141139
0.6697	Remote Similarity	NPC78041
0.6697	Remote Similarity	NPC159178
0.6697	Remote Similarity	NPC121872
0.6697	Remote Similarity	NPC209764
0.6697	Remote Similarity	NPC74936
0.6696	Remote Similarity	NPC25565
0.6693	Remote Similarity	NPC252878
0.6692	Remote Similarity	NPC199738
0.6692	Remote Similarity	NPC152850
0.6692	Remote Similarity	NPC89923
0.6692	Remote Similarity	NPC105114
0.6692	Remote Similarity	NPC71933
0.6692	Remote Similarity	NPC319766
0.6692	Remote Similarity	NPC210950
0.6692	Remote Similarity	NPC239990
0.6691	Remote Similarity	NPC262077
0.6667	Remote Similarity	NPC43755
0.6667	Remote Similarity	NPC315283
0.6667	Remote Similarity	NPC190663
0.6667	Remote Similarity	NPC130309
0.6667	Remote Similarity	NPC314388
0.6643	Remote Similarity	NPC138775
0.6642	Remote Similarity	NPC476989
0.6641	Remote Similarity	NPC165726
0.6641	Remote Similarity	NPC46427
0.6641	Remote Similarity	NPC35996
0.6641	Remote Similarity	NPC213969
0.6637	Remote Similarity	NPC473501
0.6637	Remote Similarity	NPC475439
0.6636	Remote Similarity	NPC226438
0.6619	Remote Similarity	NPC313867
0.6619	Remote Similarity	NPC316008
0.6619	Remote Similarity	NPC201244
0.6619	Remote Similarity	NPC477217
0.6618	Remote Similarity	NPC476133
0.6618	Remote Similarity	NPC92784
0.6618	Remote Similarity	NPC98424
0.6618	Remote Similarity	NPC77992
0.6618	Remote Similarity	NPC470884
0.6618	Remote Similarity	NPC178662
0.6617	Remote Similarity	NPC246079
0.6612	Remote Similarity	NPC329011
0.6607	Remote Similarity	NPC206764
0.6607	Remote Similarity	NPC58674
0.6602	Remote Similarity	NPC139901
0.6602	Remote Similarity	NPC151405
0.6596	Remote Similarity	NPC105717
0.6591	Remote Similarity	NPC325651
0.6591	Remote Similarity	NPC280807
0.6591	Remote Similarity	NPC472245
0.6591	Remote Similarity	NPC300315
0.6585	Remote Similarity	NPC471318
0.6583	Remote Similarity	NPC158854
0.6571	Remote Similarity	NPC314358
0.6569	Remote Similarity	NPC307357
0.6569	Remote Similarity	NPC46098
0.6569	Remote Similarity	NPC268841
0.6569	Remote Similarity	NPC153007
0.6567	Remote Similarity	NPC244866
0.6565	Remote Similarity	NPC218323
0.6562	Remote Similarity	NPC160493
0.656	Remote Similarity	NPC169328
0.6555	Remote Similarity	NPC142297
0.6541	Remote Similarity	NPC157311
0.6538	Remote Similarity	NPC79698
0.6538	Remote Similarity	NPC47667
0.6538	Remote Similarity	NPC474479
0.6532	Remote Similarity	NPC188010
0.6532	Remote Similarity	NPC197470
0.6525	Remote Similarity	NPC135121
0.6525	Remote Similarity	NPC311658
0.6525	Remote Similarity	NPC67043
0.6525	Remote Similarity	NPC474559
0.6522	Remote Similarity	NPC269398

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC45033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	500
0.2-0.3	947
0.3-0.4	2010
0.4-0.5	3395
0.5-0.6	1682
0.6-0.7	485
0.7-0.8	33
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7778	Intermediate Similarity	NPD4803	Discontinued
0.7706	Intermediate Similarity	NPD5103	Approved
0.7547	Intermediate Similarity	NPD4094	Approved
0.7523	Intermediate Similarity	NPD5630	Phase 1
0.75	Intermediate Similarity	NPD7130	Phase 3
0.75	Intermediate Similarity	NPD466	Approved
0.7458	Intermediate Similarity	NPD3123	Discovery
0.7455	Intermediate Similarity	NPD6588	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD742	Approved
0.7414	Intermediate Similarity	NPD480	Approved
0.7407	Intermediate Similarity	NPD4655	Approved
0.7407	Intermediate Similarity	NPD4657	Approved
0.7391	Intermediate Similarity	NPD2583	Phase 2
0.736	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD3598	Phase 3
0.7317	Intermediate Similarity	NPD2584	Suspended
0.7297	Intermediate Similarity	NPD6024	Approved
0.7297	Intermediate Similarity	NPD6027	Approved
0.7288	Intermediate Similarity	NPD3867	Phase 2
0.7288	Intermediate Similarity	NPD2508	Discontinued
0.7257	Intermediate Similarity	NPD1766	Approved
0.7257	Intermediate Similarity	NPD1761	Approved
0.7257	Intermediate Similarity	NPD1765	Approved
0.7257	Intermediate Similarity	NPD1763	Approved
0.7257	Intermediate Similarity	NPD1767	Approved
0.725	Intermediate Similarity	NPD5990	Approved
0.725	Intermediate Similarity	NPD5991	Approved
0.7245	Intermediate Similarity	NPD4147	Approved
0.7245	Intermediate Similarity	NPD4144	Approved
0.72	Intermediate Similarity	NPD3125	Approved
0.72	Intermediate Similarity	NPD5578	Approved
0.72	Intermediate Similarity	NPD2031	Discontinued
0.72	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD998	Approved
0.719	Intermediate Similarity	NPD6345	Approved
0.719	Intermediate Similarity	NPD6343	Approved
0.7188	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2124	Approved
0.7155	Intermediate Similarity	NPD3581	Discontinued
0.7143	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD813	Approved
0.7143	Intermediate Similarity	NPD3551	Approved
0.7143	Intermediate Similarity	NPD5631	Phase 3
0.7132	Intermediate Similarity	NPD2846	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8643	Discontinued
0.7094	Intermediate Similarity	NPD3643	Approved
0.7094	Intermediate Similarity	NPD3642	Approved
0.7094	Intermediate Similarity	NPD3644	Approved
0.709	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7086	Phase 2
0.7063	Intermediate Similarity	NPD6792	Phase 3
0.7034	Intermediate Similarity	NPD753	Approved
0.7031	Intermediate Similarity	NPD3626	Phase 3
0.7025	Intermediate Similarity	NPD1344	Phase 2
0.7025	Intermediate Similarity	NPD7679	Phase 2
0.7	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD2648	Phase 3
0.6991	Remote Similarity	NPD2171	Approved
0.6991	Remote Similarity	NPD2193	Phase 2
0.6991	Remote Similarity	NPD4119	Approved
0.6985	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4677	Discontinued
0.6983	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4125	Approved
0.6967	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4027	Approved
0.6961	Remote Similarity	NPD4026	Approved
0.6957	Remote Similarity	NPD999	Phase 2
0.6957	Remote Similarity	NPD1018	Approved
0.694	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1100	Approved
0.6937	Remote Similarity	NPD1099	Approved
0.6935	Remote Similarity	NPD6806	Phase 1
0.693	Remote Similarity	NPD3357	Discontinued
0.6923	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5859	Discontinued
0.6905	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4169	Approved
0.6893	Remote Similarity	NPD4170	Approved
0.6893	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4117	Approved
0.6875	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5157	Phase 1
0.685	Remote Similarity	NPD5159	Phase 2
0.6847	Remote Similarity	NPD2895	Discontinued
0.6842	Remote Similarity	NPD4818	Approved
0.6842	Remote Similarity	NPD4817	Approved
0.6842	Remote Similarity	NPD2196	Discontinued
0.6838	Remote Similarity	NPD7720	Phase 2
0.6825	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4478	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1948	Approved
0.6815	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD787	Suspended
0.681	Remote Similarity	NPD5717	Approved
0.6807	Remote Similarity	NPD5927	Discontinued
0.6803	Remote Similarity	NPD1323	Discontinued
0.6797	Remote Similarity	NPD6325	Discontinued
0.6797	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3035	Approved
0.6792	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4658	Approved
0.6783	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4656	Approved
0.6777	Remote Similarity	NPD5179	Approved
0.6777	Remote Similarity	NPD5181	Approved
0.6777	Remote Similarity	NPD5180	Approved
0.6772	Remote Similarity	NPD3071	Approved
0.6772	Remote Similarity	NPD3072	Approved
0.6772	Remote Similarity	NPD3073	Approved
0.6769	Remote Similarity	NPD1781	Discontinued
0.6767	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8416	Discontinued
0.6762	Remote Similarity	NPD2539	Approved
0.6762	Remote Similarity	NPD5178	Approved
0.6762	Remote Similarity	NPD2538	Approved
0.6761	Remote Similarity	NPD7131	Phase 3
0.6757	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1947	Approved
0.6742	Remote Similarity	NPD5581	Approved
0.6742	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7230	Approved
0.6741	Remote Similarity	NPD7231	Approved
0.6741	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1724	Approved
0.6724	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4102	Approved
0.672	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5981	Approved
0.672	Remote Similarity	NPD4105	Approved
0.672	Remote Similarity	NPD6994	Approved
0.672	Remote Similarity	NPD6993	Approved
0.6718	Remote Similarity	NPD5263	Approved
0.6718	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3908	Approved
0.6716	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5716	Approved
0.6693	Remote Similarity	NPD4762	Approved
0.6693	Remote Similarity	NPD4761	Approved
0.6692	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD941	Approved
0.669	Remote Similarity	NPD7613	Discontinued
0.6667	Remote Similarity	NPD4164	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4733	Approved
0.6667	Remote Similarity	NPD1025	Discontinued
0.6667	Remote Similarity	NPD2197	Approved
0.6667	Remote Similarity	NPD2192	Approved
0.6667	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8173	Phase 2
0.6667	Remote Similarity	NPD8172	Phase 2
0.6667	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5675	Discontinued
0.6667	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4635	Approved
0.6644	Remote Similarity	NPD6726	Phase 2
0.6644	Remote Similarity	NPD6725	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD8323	Discontinued
0.6643	Remote Similarity	NPD7575	Phase 3
0.6642	Remote Similarity	NPD6623	Phase 3
0.6641	Remote Similarity	NPD3040	Approved
0.6641	Remote Similarity	NPD6408	Phase 1
0.6638	Remote Similarity	NPD4231	Approved
0.6638	Remote Similarity	NPD3682	Approved
0.6638	Remote Similarity	NPD3680	Approved
0.6638	Remote Similarity	NPD4229	Approved
0.6637	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4406	Approved
0.6636	Remote Similarity	NPD4636	Approved
0.6636	Remote Similarity	NPD4409	Approved
0.6618	Remote Similarity	NPD6901	Phase 3
0.6617	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1330	Phase 2
0.6615	Remote Similarity	NPD5653	Discontinued
0.6614	Remote Similarity	NPD4135	Approved
0.6614	Remote Similarity	NPD4106	Approved
0.6614	Remote Similarity	NPD4136	Approved
0.6613	Remote Similarity	NPD5162	Approved
0.6613	Remote Similarity	NPD4574	Approved
0.6613	Remote Similarity	NPD4576	Approved
0.6612	Remote Similarity	NPD4991	Discontinued
0.6594	Remote Similarity	NPD4152	Approved
0.6591	Remote Similarity	NPD4620	Approved
0.6591	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4617	Approved
0.6591	Remote Similarity	NPD5203	Approved
0.6591	Remote Similarity	NPD5201	Approved
0.6585	Remote Similarity	NPD2543	Discontinued
0.6583	Remote Similarity	NPD1756	Approved
0.6583	Remote Similarity	NPD5236	Approved
0.6583	Remote Similarity	NPD5240	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data